1. Round | 10/07/2016 | Carolina RailHawks | - | Tampa Bay Rowdies | 4:1 | ||||
1. Round | 17/07/2016 | Tampa Bay Rowdies | - | Puerto Rico FC | 3:0 | ||||
1. Round | 31/07/2016 | Ottawa Fury | - | Tampa Bay Rowdies | 2:0 | ||||
3. Round | 11/09/2016 | Tampa Bay Rowdies | - | Puerto Rico FC | 0:0 | ||||
4. Round | 30/10/2016 | Jacksonville Armada | - | Tampa Bay Rowdies | 3:2 |